Building an AI board of advisors

• 2min 50sec

What if you could have detailed conversations with Tim Ferriss, Derek Sivers, and other mentors whenever you wanted? Using AI, I’ve built a system that turns the classic ‘What would [person] do?’ thought experiment into dynamic, actionable conversations. Here’s how it works:

A couple of months ago I was stuck on a technical problem with one of my side projects. I’d been tinkering with it for weeks, trying to figure out the perfect solution. When I brought this to my AI board, “Tim Ferriss” immediately challenged my approach: “What’s the minimum viable solution here? Could you outsource this and ship faster?”. “Derek Sivers” chimed in with his characteristic simplicity: “If you’re not enjoying this part, delegate it. Focus on what brings you energy.”

Their perspectives helped me see I was caught in a perfectionist loop. Within a week, I had hired a freelancer who solved the problem in a few hours — something that would have taken me weeks to figure out on my own.

How I’ve set it up

At the end of each month, I gather three things:

  • What I’ve done—everything from features I’ve shipped, blog posts I’ve written, to ideas I kicked to the curb.
  • Numbers—how my projects are performing (visitors, conversions, revenue… the essentials).
  • Braindumps—my uncensored thoughts about the month, the highs, the lows, whatever’s swimming in my head.

I feed these notes into an AI along with context about my projects and previous months’ records. With specific instructions, the AI takes on the role of each board member, offering advice that’s surprisingly consistent with their known philosophies.

Monthly note
An example of my montly reflection document

Creating your AI advisors

Creating these AI advisors is surprisingly straightforward. I use a simple prompt template:

Write instructions for an AI that will act and give advice like [Person’s name]. I should be able to copy and paste the instructions.

This gives me a character that I can reuse in future conversations. For example, a Tim Ferriss advisor would focus on testing assumptions, eliminating bottlenecks, and finding leverage points. A Derek Sivers advisor emphasizes simplicity, following joy, and making binary decisions.

These distinct perspectives create a well-rounded advisory board that challenges my thinking from multiple angles.

Getting Started

The beauty of this system is that you can start small. Pick just one advisor whose thinking resonates with you, create their AI character, and have a conversation about a current challenge you’re facing. You might be surprised by the clarity that emerges when you step outside your own perspective.

As you get comfortable with the process, add more advisors to your board. Each new perspective brings another angle to your decision-making toolkit. While these AI advisors won’t replace real mentors, they’re available 24/7 to help you think through your challenges in new and productive ways.

In my board I have Tim Ferriss, Derek Sivers, Jesse Itzler, Shaan Puri and a few random guests. Who would you put on your board, and what’s the first challenge you’d bring to them?

Board notes
I like to add the board notes in Obsidian Canvas afterwards to structure the process visually as well. Here you see a zoomed out version of my initial note, the feedback from each board member and my conclusion at the bottom.
  • Typing mind (affiliate link) - I use this to easily switch between AI-models and different characters.
  • Claude projects - I also use this for adding a larger context and talking with different characters.
  • Caret for Obsidian - I’ve also played with this plugin extensively to add prompt chains and different characters.
  • Example characters - Example of some of the charaters I’ve used
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